Water → HCID 89543798, compound

HRID 509453Notes

Reaction equation

HRID 509453 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:17](=[O:18])[C:12]=3[O:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[NH:19][CH:20]=[O:21].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:29][C:30](=[O:32])[CH3:31].O>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:17](=[O:18])[C:12]=3[O:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[N:19]([CH2:29][C:30](=[O:32])[CH3:31])[CH:20]=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 89543743HCID 89543743, compound

Product 1

HCID 89543798HCID 89543798, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of N-(2-methoxy-4-(7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-yl)phenyl)formamide (2.66 g, 9.28 mmol), Cs2CO3 (5.37 g, 27.9 mmol), and KI (308 mg, 1.86 mmol) in dry DMF (40 ml) was added chloroacetone (7.72 g, 18.57 mmol) dropwise. The reaction was stirred at 55° C. over night. Reaction mixture was worked up with water and DCM, organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The product was purified by chromatography on silica gel using a mixture of ethyl acetate and hexanes as the eluent to furnish 1.05 g of the title compound, MS(M+H)+=343.

Workup

  1. customReaction mixture
  2. washwas washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was purified by chromatography on silica gel using
  6. additiona mixture of ethyl acetate and hexanes as the eluent

Sources & evidence

ORD record
ord-aa41e9541d1b48539f28a508596d661d
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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